Over the years, The Simpsons has gone from being probably the best TV show broadcast to a shambling version of itself. This downslide has led to what critics call “zombie Simpsons,” thought of as airing from around 2000. While there have been some good episodes of the show since, with “Midnight RX” a personal favorite, by and large, it never matches the majesty it achieved 20 years ago. From pointless celebrity cameos that do nothing except worship at the altar of celebrity that The Simpsons used to so fiercely parody, to countless episodes grappling with modern technology, it is a show that has outlived itself.
If you truly want to understand why, the best explanation on this that I’ve ever seen can be found here, but I’ve got a few ideas of my own. The Simpsons is a show that depends heavily upon its writers. When the writing staff was at its absolute best under Conan O’Brien, they consistently put out some of the most hilarious, heartwarming television ever made. Now, it’s dwindled, with most of the original writing staff has since departed. As such, there’s no lineage that keeps the show consistent, with writers coming in and messing with the characters in ways that make no sense. The other big problem with the show is that its characters and situations are firmly rooted in the eighties. Lisa being mocked as a nerd makes no sense in today’s world, where nerd culture is huge, for example. Here are 30 episodes where The Simpsons went badly wrong.
27 The Principal And The Pauper
Widely regarded as one of the biggest missteps The Simpsons ever made, this episode from season 9 messes with one of the fans’ favorite characters. In it, we discover that Principal Skinner is not actually Principal Skinner, and is instead, a reformed street punk called Armin Tamzarian. According to the show, he took on Skinner’s identity having believed he was defeated in combat. The problem with this is that a huge amount of development went into Skinner. Fans loved the authoritarian, cranky, but above all, caring Skinner, and this single episode destroyed his character.
26 Moe Goes From Rags To Riches
Want an episode that really goes off the rails? Here you go. Fundamentally, The Simpsons has always been somewhat based in reality. A stylized, silly reality, sure, but reality nonetheless. Then you get this episode. Here, Moe’s bar rag is revealed to be sentient and capable of speech, and it proceeds to tell the story of its life. I really really wish I was kidding. Moe eventually has the rag stolen, before discovering it was Marge who took it and cleaned it. Moe ditches the rag after finding love with the Simpsons and the rag is taken in by Santa’s Little Helper.
25 Clown In The Dumps
There are many things wrong with this episode. First and foremost, there’s the fact that the death of a character, so extremely well dealt with in the case of Bleeding Gums Murphy, was ghoulishly hyped up. Then there’s the fact that the death in question is not so nearly gracefully dealt with. Look at how Krustofski’s death is handled compared with Lisa playing a duet with the spirit of Murphy. How are these even the same show? It’s an insultingly bad use of grief as a storytelling technique, and was thoroughly out of place.
24 All Singing, All Dancing
One of the very few episodes from the classic era on this list, All Singing, All Dancing is pointless. For once, Homer is a voice of reason, complaining about how bad musicals are at the beginning of a musical episode. Surely, someone with half a brain on the writing team should have noticed this irony. The worst part of the episode is that the songs in the episode are from earlier episodes, making it, essentially, a clip show. These are never good.
23 The Musk Who Fell To Earth
Do you remember back in the day when Elon Musk seemed new and exciting? In those days, he was guest starring in The Simpsons. If this episode licked his boots more it would be on an entirely different kind of TV channel. Musk is cast as essentially a heroic figure who is on a mission to save the Earth. He’s depicted as not caring about money (evidently untrue), provides Springfield with unlimited power, has Homer save his life, then boards a rocket into space. Yikes.
22 What To Expect When Bart’s Expecting
Look at that title. Tell me it makes any sense in The Simpsons canon. It’s “wacky” Simpsons at its absolute worst. Bart makes a voodoo doll of an art teacher and casts a spell on her to make her sick, but ends up getting her pregnant. Bart ends up opening a clinic serving the couples of Springfield. He is then taken to work his voodoo magic on a champion racehorse. That’s it. That’s the episode: Bart becomes a voodoo priest (essentially) and is also stolen.
21 Gump Roast
This episode begins with a reference to Forrest Gump, with Homer sat on a parkbench with a box of chocolates. Homer uses flashbacks to tell Chief Wiggum a story, before going to the Friars Club, where is roasted by various people using, you guessed it, more clips we’ve already seen before. It goes on in this vein for a long, long time. The real insult of this episode is that it ends with a song that contains an apology for the clip show. They knew these episodes were unpopular, yet did it anyway.
20 Sweets And Sour Marge
This is a really bad episode for a couple of reasons. It’s loosely based on the film Erin Brokovich, but then goes down a crazy rabbithole. It features an Oompa-Loompa, for chrissakes. The most fundamental problem with this episode is that it does nothing we’ve not seen several times before, and done far better. It hinges upon Marge being a campaigner against fairly popular things, which has been done in Marge Vs. The Monorail and Itchy & Scratchy & Marge. It’s just weak, so very weak.
19 The Homer They Fall
This is probably the strongest episode on this list. It’s not terrible, but I include it because it marks the first appearance of a serious problem. It’s where The Simpsons started to become a cartoon, rather than a sitcom that happened to be animated. The episode is a parody of countless boxing movies, with Homer somehow rising to the top of the pile and challenging Drederick Tatum in his comeback fight. It’s profoundly strange, and the worst part is Moe playing a literal Deus Ex Machina role, flying in on a paramotor and rescuing Homer before flying away.
18 The Great Phatsby, Parts 1 And 2
A phenomenally unnecessary two-part episode, The Great Phatsby is stupid. Parodying Empire and The Great Gatsby, it tries to mix hip-hop and the classic novel, and fails incredibly badly. They managed to rope in some of the biggest names in hip-hop to cameo, including Beyonce, Snoop Dogg, and RZA, but it’s just not at all funny. It seems like an episode that was made exclusively to be able to point at the cameos they could get, while the fact it’s a two-parter is a ridiculous self-indulgence that serves no purpose at all.
17 Lisa’s Wedding
I feel like I’m going to get some hatred for this, but hey, let’s go. Yes, it’s from one of the greatest seasons of the show, but it just doesn’t work. I have a big problem with episodes that jump into the future just because they feel somewhat lazy. Using similar storylines that have already been used, just on older versions of the characters, isn’t clever scriptwriting. Yes, it’s got a nice little gut-punch of emotion, but it doesn’t come close to what other episodes have been able to deliver.
16 Yellow Subterfuge
This is an episode that takes the heart The Simpsons used to have and drives a knife clean through it. It revolves around Skinner, who, as we know, loves and dotes on his mother despite her ill-treatment of him. Yet in this episode, Bart and Homer play a staggeringly cruel prank upon him, staging her brutal murder and framing Skinner for it. However, it is gone all along. Meanwhile, a B story focuses on Krusty going bankrupt in strange circumstances. It’s not a classic episode, let’s say that.
15 Every Man’s Dream
That title is so tacky. It suits the episode down to the ground, as it is by far and away the tackiest episode of The Simpsons ever made. It takes the “will they break up” question about Marge and Homer to a whole new level, with them finding new partners. It becomes a tangled mess of interweaving relationships, which just causes the episode to trip over itself. Marge agrees to marry her new beau, and Homer’s gets pregnant. Then it’s revealed that this is all a dream, or more accurately, a dream within a dream within a dream. Stupid.
14 Homer Vs. Dignity
Of all the stupidest episodes of The Simpsons, this is the stupidest. It doesn’t just ruin Homer’s dignity, it ruins the show’s dignity. It recycles plot motifs from four or five earlier, far better, Simpsons episodes. It also has the most degrading, outright mean-spirited scene in an episode. Homer is employed as Mr. Burns’ “prank monkey,” who has to carry out various humiliating tasks? How it culminates is not suitable for this website, but let’s just say that Homer is “assaulted” by a panda at the zoo, and leave it at that.
13 Blame It On Lisa
From one pointless exercise in scene-shifting to another, Blame It On Lisa sees them go to Brazil. Woop de doo. Again playing upon every stereotype going, Brazil is portrayed as a mad land filled with thieves. Homer and Bart are taken and ransomed off. Then, when they end up paying the ransom, Homer jumps between a pair of cable cars, snaps the rope, and then Bart gets eaten by an Anaconda. He then proceeds to start dancing in the Brazilian stylee while inside the snake. What.
12 That 90s Show
This is an episode of the show that doesn’t so much retcon Simpsons history as throw it in the garbage. Instead of getting together in the 70s, Homer and Marge are instead discovered to have gotten together in the 1990s, when Homer played in a grunge band called Sadgasm. The show parodies various grunge songs, badly, and then Homer and Marge conceive Bart in a mini-golf course, just like they did in an earlier episode, in the 1970s. This was absolutely unnecessary, The Simpsons already has a floating timeline, why mess with it?
11 Homer The Moe
One of the first Simpsons episodes to essentially reuse an earlier plot point, this episode shamelessly rips off Flaming Moes. Both play upon Moe’s changing fortunes, with the tavern rebranding into a fancy club called M. It features REM for no real reason, plays with suicide as a joke, and also has Moe going back to Swigmore University. The episode just feels completely pointless, and completely lacks the wit and magic of Flaming Moes. If you can’t come up with an original plot, cancel the show.
10 Day Of The Jackanapes
Yet another instance of The Simpsons becoming wacky, rather than actually inventive or humorous. Day of the Jackanapes is a parody of The Manchurian Candidate. After all old episodes of the Krusty the Klown Show with Sideshow Bob are erased, Bob hypnotizes Bart into carrying out a bombing during a live taping of the show. As well as featuring a premise that could be described as in bad taste at best and offensive at worst, it’s just plain silly. It ends with Sideshow Bob being threatened with the Guillotine for heaven’s sake.
9 E Pluribus Wiggum
A parody of politics that just doesn’t really work. If you want political satire from The Simpsons, look at Mr. Lisa Goes To Washington, or Last Exit To Springfield. Instead of actually satirizing something that could happen in the real world, this episode takes it to the ne plus ultra, having Ralph Wiggum win a Primary. Everyone then fights for his approval, with them both eventually coming together in their support of Ralph. It’s saccharine sweet enough to rot your teeth while also being stupid enough to destroy your brain.
8 MyPods And Boomsticks
Hey guys, do you get the joke? A MyPod sounds like an iPod! What a clever gag. That’s not even really the most offensively bad part about this episode. Homer is once again depicted as mean-spirited, being suspicious of Bart’s new Muslim friend Bashir for no reason whatsoever. Oh, by the way, the company that makes the MyPod is called Mapple, and it’s run by Steve Mobbs. Where did the wit go? In its place we’re left with an Aral Sea of wit, just a dried up stain of what the show used to be.
